Pharmaceutical products



Patented Sept. 25, 1928.

UNITED STATES P 1,685,341 ATENT, OFFICE- wALrER'scHoE LER," ADOLF FELDTQMAX GEHRKE, Ann' nmc'n 'nonewann'r, or BERLImaeERMA Y, ASSIGNORS TO THE FIRM: VCHEMISCHE FABRIK AUF AcTIniir (VQRM. E. SCHERIN G),

No Drawing. Application filed May 9, 1925, Serial No. 29,207; and in Germany June Our invention refers to pharmaceutical products and more'especially to products obained from amino metal mercapto benzene compounds; it further refers to the methods of making such products. The. new products are distinguished from the amino metal mercapto benzene compounds by agreater stability of the watery solutions of their salts and by a. more favorable chemotherapeutical coefficient. lVe preferably obtain them by causing acylizing agents, such as anhydrides, halides or the like, of acids to act on theconpounds mentioned above in the form of'their acids or salts.

than phosgen is employed, the new products correspond to the formula i i S-Me Ar-X-Y J NH-acyl w herein Ar is a benzene nucleus, Me a heavy metal, X=COO 0r S0 and Y=either H or aimetal, preferably an alkali metal. Acyl 1 y. be a saturated or non-saturated acid radical.

The new products are not easily soluble in water as acids, but easily soluble therein as alkali salts. In both forms they are soluble in alcohol only with difiiculty. They are distinguished by their action on spirochaetae, more especially on spirochaeta pallida. and recurrens. In their gold and silver compounds the metal forms part of acomplex compound and cannot be traced by means of the usual precipitating agents. The new products are preferably uscd'in the form of their soluble salts, more especially sodium salts, by subcutaneous or intravenous injection.

In producing the new compounds according to the present invention we preferably proceed as follows:

Example 1.28 grams of the 4-amino-2- argento mercapto benzene-l-carboxylic acid (see for instance U. S. Patent 1439624) are suspended in 200 ccms. water and a 10 per cent soda solution is added drop by drop until solution begins and a. weak alkalin reaction is obtained. 12 ccms. acetic acil anhydride are now added to the mixtrue andistirred until the NIL group can no .more ice traced. The free acid which is formed is well rinsed and is then dissolved in the exact quantity of soda required for solu- Provided that an acylizing agent other 0F BERLIN, GERMANY.

PHARMACEUTICAL PRODUCTS.

tion, whereupon the sodium salt of 4-acetyl ammo-2?.argento, mercapto benzene-Learboxyhc acid -OOONa SAg v I NH-CO-OH: is precipitated with alcohol. Aftersome time another considerable portionis'obtained in the form of a micro crystalline powder." The product has a whitish-yellow color and is easily soluble in waterQ The watery solution showsa neutral reaction. i

Example 2-77 grams 4-amino-2-auro mercapto benzened-carbo'xylic sodium are shaken in watery solution with an etheric solution of grams meta-nitro benzoyl chloride. The condensation product thus formed is separated by filtration, rinsed with hot water and thereafter with ether and reduced with ferrous salt in alkaline solution. After removing the iron sludge and acidifying with dilute hydrochloric acid there is obtained the 4-meta-amino benzoyl-amino-Q-auro mercapto benzene-l-carboxylic acid, which forms a greenish grey deposit soluble in dilute alkalis.

If other amino metal inercapto benzene compounds or their salts are employed, the process will give analogous results.

l/Ve wish it to be understood'that we do not desire to be limited to the exact substances, proportions, conditions and sequence of operations above described, for obvious modifications will occur to a person skilled in the art.

In the appended claims the term acid is designed to include-also the soluble salts of the respective acids.

. e claim 1. As a new product, the derivative of an amino metal mercapto compound corresponding to the formula sMe' NH-AcyI wherein Ar is a benzene nucleus, Me is a heavy metal, X is COO, Y is hydrogen or a metal, more especially an alkali metal, such product dissolving in water only with difficulty as an acid, readily as. an alkali salt and having a therapeutical effect more espetives of amino .metal 5. The method of producing new derivatives of amino metal mercapto compounds, consisting in, acting on an amino mercapto benzene compound first with an acylizing agent'and thereafter introducing a metal into the sulfhydryl group.

6 As new products the acetyl-amino metal mer'capto benzene carboxylic acids and their salts corresponding to the formula.

wherein Ar is a benzene nucleus, Me is a heavy metal, Y is hydrogen or an alkali metal, such product dissolving in water only with difficulty as an acid, readily as'an alkali saltand havinga therapeutical eflect more especially in cases caused by spirochze tm. I 4 r V v- V,

j 7. As new products the acetyl amino auro mercapto benzene carboxylic acids and their salts corresponding-to the formula SAu Ar-OOOY NH-COCHa V v wherein Ar is a benzene nucleus, Y is hydrogen or an alkali metal. such product dissolving in Water only with difiiculty as an acid,

readily as an alkali salt and having a therapeutical effectmore especially in cases caused by spirochaatze. r v I r 8. The methodof producing new derivatives o'famino'metal m'ercapto compounds, comprising acting on an amino metal mercapto benzene carboxylic acid with an acyliz- 'ing agent;

In testimony whereof we aflix our tures. V

WALTER SCI-IOELLER.

ADOLF FELDT. MAX GEHRKE. ERIGH ,BORGWVARDT.

signa- 

